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8 Tips to Style Men’s Dress Shirts from Day to Evening

September 07, 2023

8 Tips to Style Men’s Dress Shirts from Day to Evening

It might be hard to fathom as we push through the final hot days of summer, but fall is upon us, with winter not far behind. With this change of the weather comes event season. It’s that time of the year when your calendar fills up with fall get-togethers, holiday parties, happy hours, and more. That means you’ll also have less time to head home between the day’s activities to change.

Being able to take a work outfit from day to night is a necessary skill for this time of year (and any busy season in life!). Mastering this skill is a game-changer - it can take you from feeling self-conscious and overdressed to confident and in control. Here’s how.

8 Tips to Re-Style Your Dress Shirt

1. Choose a Comfortable Cut

There are several styles of dress shirts: slim, classic, and modern. Slim is the tightest and classic is the baggiest, with modern somewhere in between. If you’re planning on wearing your dress shirt from day to night, you’ll want to choose a comfortable cut that will look good all day.

A fit that’s too tight will be constricting and may end up with odd creases as you wear it throughout the day. A classic fit can get wrinkly and stretch to become even bigger than before. Meanwhile, a modern-cut dress shirt that actually fits you properly will stay sharp throughout the day. Having the proper fit will ensure you look good and have a solid foundation from which you can work.

2. Consider Your Pattern

Patterned Mens Dress Shirt

Patterns are just one way to have fun with your dress shirt. You can play up the pattern and match it to your tie and socks - which looks great with your work suit. However, if you plan to transition that same shirt to an evening affair, you risk looking a little goofy. Why? If you take off your jacket and go with the dress shirt and pants look, your shirt, tie, and socks could seem loud without the solid color of the jacket toning it all down.

That’s not to say you should avoid patterns altogether. Just be sure to consider how the chosen pattern will look in the evening. Choosing a more subtle or casual pattern can work well. For example, a wider plaid print can look nice under a jacket and look good on its own without a jacket. Meanwhile, a small gingham print could look too busy without a jacket. Likewise, a subtle single-tone print will read more like a solid, clean dress shirt in a dark bar. In comparison, a loud multi-color pattern could look more obnoxious.

3. Use Buttons Wisely

What do you do at the end of a long day in formal wear? You remove your tie and unbutton the first couple of buttons on your shirt. You can follow this same rule as you transition from a formal day at work to a night out with friends.

In general, unbuttoning the top two buttons is acceptable for just about any casual event. If you really want to look relaxed, you can unbutton a third.

4. Tuck and Untuck

Men's Salmon Color Jacket with Solid Dress Shirt

If you want to dress down, untucking your dress shirt can be the perfect move to look cool and relaxed. There is one important consideration here though - shirt length. If the shirt is long enough to cover your pants pockets, it’s too long to wear untucked. Untucked shirts should hit no lower than just above those butt pockets. On the other hand, if your shirt is too short and you try to tuck it, you’ll notice the hem popping out unexpectedly.

All of that to say, if you plan to untuck your shirt after a long day at the office, make sure it hits you at the right spot on your body. Vice versa, if you want to wear a casual dress shirt untucked during the day and then tuck it in for a more formal event at night, make sure it’s long enough to stay tucked in.

5. Cuff It

This tip is simple. If you’re going for a casual vibe - say an evening at a bar - consider rolling your sleeves up. Just be sure to do it cleanly. You’ll want to unbutton the wrist button but keep the one that’s closer to your elbow buttoned. Flip the cuff back once and then double it over. The cuff should hit your mid to upper forearm.

6. Add a Sweater

If you want to look polished but not too dressy, putting a sweater over your dress shirt can be the perfect solution. Swap out your suit jacket and tie for a good quality crew neck sweater.

It’s generally best to keep your dress shirt buttoned to the top, though you may choose to unbutton one button for comfort. Keep the collar tucked into the shirt for the cleanest look. You can find more tips on choosing the right sweater in our fall style guide.

7. Swap Jackets

Green Men's Jacket

If you’re headed to a more formal event, you may want to maintain a dressy appearance. However, some suit jackets appear more business-forward rather than formal. Patterned suit jackets tend to be better for work rather than formal events. Likewise, the smoothness and shine of the fabric will also play a role - smoother and shinier fabric looks more formal.

With that in mind, you can bring a second jacket in your car to adjust for the occasion. You might go from wearing a patterned jacket at work to a solid color, smoother jacket for a high-end holiday party, for example. Just make sure the new jacket matches or compliments your shirt and pants.

8. Swap Pants

You can always swap your pants out to dress your shirt up or down. Slacks and dress pants are more formal, while chinos, khakis, and jeans are on the casual end. This simple swap can drastically alter your look, making it an easy way to adjust to changing events.

For example, don’t be afraid to keep a pair of clean, dark-wash denim in your car. Throw those on, remove your tie, and unbutton the top button of your dress shirt and you’re ready for a casual event!

Looking for new dress shirts to carry you through your busy schedule? Check out the latest styles in men’s shirts at Franky Fashion.

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